Takeuchi Toshifumi, Shibasaki Masakatsu
Institute of Microbial Chemistry (BIKAKEN), Tokyo 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
Org Lett. 2024 Sep 20;26(37):7981-7986. doi: 10.1021/acs.orglett.4c03085. Epub 2024 Sep 10.
This study reported a copper-catalyzed direct asymmetric aldol reaction between aldehydes and glycine Schiff bases with methyl, allyl, and -butyl esters. Additionally, this reaction afforded high yields of -β-hydroxy-α-amino esters with excellent enantio- and diastereoselectivities (93-99% ee, up to >99:1 dr). The aldol reaction accepted aromatic, linear aliphatic, and α-substituted aliphatic aldehydes.
本研究报道了一种铜催化的醛与甘氨酸席夫碱之间的直接不对称羟醛缩合反应,该反应涉及甲酯、烯丙酯和丁酯。此外,该反应能以高收率得到β-羟基-α-氨基酯,且对映选择性和非对映选择性极佳(对映体过量值为93 - 99%,非对映体比例高达>99:1)。该羟醛缩合反应适用于芳香醛、直链脂肪醛和α-取代脂肪醛。